Methanol → 8-Azabicyclo(3.2.1)octan-3-one

Temperature

60 °C

To a stirred solution of ethyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (500 mg, 2.53 mmol) in 1,2-dichloroethane (10 mL) was added 369 μL (2.60 mmol) of trimethylsilyl iodide (TMSI) under a nitrogen atmosphere. The reaction mixture was heated at 60° C. for 4 h and cooled to room temperature. Methanol (10 mL) was added and the mixture was stirred for 30 min at room temperature (rt). The solvent was removed on vacuo and the residue was partitioned between CH2Cl2 and 1M aqueous NaOH solution (5 mL). The mixture was extracted with CH2Cl2 (3×10 mL). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, methylene chloride/EtOH/NEt3 85/10/5) to afford a pale yellow oil (140 mg, 44%).

1. temperaturecooled to room temperature
2. customThe solvent was removed on vacuo
3. customthe residue was partitioned between CH2Cl2 and 1M aqueous NaOH solution (5 mL)
4. extractionThe mixture was extracted with CH2Cl2 (3×10 mL)
5. dry with materialThe organic layers were dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude material was purified by flash chromatography (silica gel, methylene chloride/EtOH/NEt3 85/10/5)

ORD record

ord-b8f9395ae15c4e18b9197e3870cde752

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637496B2